


Sharpdene's Night Out

by StrongBrush1



Category: Homestar Runner
Genre: Crossdressing, F/M, Gender or Sex Swap, Hermaphrodites, Loss of Virginity, M/M, Magical Pregnancy, Other, Transformation
Language: English
Status: Completed
Published: 2017-08-16
Updated: 2017-08-16
Packaged: 2018-12-16 05:25:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,792
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11822121
Author URL: https://archiveofourown.org/users/StrongBrush1/pseuds/StrongBrush1
Summary: On a lonely Friday night, Strong Bad decides to head to the club in disguise as "Sharpdene". Little does he know, he's in for the most eventful night of his life.





	Sharpdene's Night Out

**Author's Note:**

> WOW, I'm behind on my writing schedule for this year. Well, in celebration of the glorious return of Strong Bad Email (at least until H*R goes on hiatus for 6 more years), have a big gay fan fiction that's full of casual weirdness. For the record, I actually wrote this BEFORE sbemail 207 came out, but for some reason didn't post it until now. Hope you enjoy it.

SHARPDENE’S NIGHT OUT

A Homestar Runner Fan Fiction (Because I Have Time to Say All Three Syllables)  
By Vavian “Strongbrush” Free

Strong Bad filed through his inbox, as he had done thousands of times before on a lonely Friday night. There were only so many times he could hit the delete key before the wonderful sound that the Lappier made when deleting emails started to wear out its magic.  
“Another Friday, another cleaning of the inbox. Jeez St. Jeezum, I’m bored.”  
Strong Bad decided to let the Lappier rest for a moment. He reached for his newly acquired Nokia 3310 and checked it for messages. None. Strong Bad went to put the phone back. But just then:  
Ding dong!  
Strong Bad put his cell phone in his pants and rushed down the stairs to the front door. He HAD to know who in the crap was at his house on a Friday night.  
Strong Bad opened the door. To his surprise, Pom Pom was standing outside.  
“Pom Pom? What are you doing at my house?”  
Pom Pom bubbled a short, concise answer.  
“You’re here for a date? But… there aren’t any attractive ladies in my house that I’m aware of.”  
Pom Pom bubbled his way through an explanation.  
“I’m sorry, I must not have heard right. You’re having a date with who?”  
“Is Pom Pom at the door?” asked a dumpy voice from upstairs.  
“Yes, Strong Sad. He says he’s here for a date with some girl whose name sounds suspiciously like yours.”  
“Oh boy. I’ll, uh, I’ll be out in a minute.”  
“Would you excuse us? Ella-phant Enchanted needs a moment.”  
Strong Bad went back upstairs to have a talk with his younger brother through the bedroom door.  
“Okay, Strong Sad. I need an explanation, because Pom Pom’s not making any sense. He says he’s here for a date, but I would know if there were any hot ladies around. So what gives?”  
Strong Sad took a deep sigh. “He’s not here for a lady. He’s going on a date with me.”  
“Okay, see, I thought he might have said something like that, but that can’t possibly be true.”  
“But it is.”  
“No, it isn’t. I know Pom Pom. Pom Pom is a friend of mine. And Pom Pom likes ladies.”  
“He likes ladies AND guys. He’s bisexual!”  
“Wait. buy-what? Is that a thing that exists?”  
“You’re not surprised I’m gay, but you didn’t know about bisexuality?”  
“Oh, believe me, I had my suspicions from the VERY beginning about you. But… I didn’t know you could be gay and straight at the same time.”  
“It’s more common than you think. A ton of people we know are bi.”  
“Really? Like who?”  
“Well, in addition to Pom Pom, there’s Bubs, Coach Z, Homestar, Marzipan… even Homsar.”  
“Wow. Suddenly… things are making sense a bit.”  
Strong Sad opened the door, wearing guyliner and a hot pink Sloshy t-shirt. “I’m glad I could enlighten you. We’re going to Club Technochocolate, so I won’t be home for a while. How do I look?”  
“Like a gay weather balloon.”  
“Good enough for me!” Strong Sad went downstairs to greet Pom Pom, leaving Strong Bad all alone upstairs.

Strong Bad walked back into the computer room, confused. “I don’t understand it. How does my loser little brother have a boyfriend and I don’t? Not that I really want a boyfriend. I mean, I don’t. Do I? No, no… I don’t.”  
Strong Bad heard a series of “meh” noises behind him. The Cheat had somehow snuck in without him noticing.  
“The Cheat! I was, just, uh, NOT talking to myself about Strong Sad. and his… bicycles.”  
The Cheat spoke again, accusingly this time.  
“Jealous? I’m not jealous, why should I be jealous of Ex-President Sad Sackery Taylor and his super cool boyfriend that nobody told me about?”  
The Cheat stared daggers through Strong Bad, raising one of his eyebrows.  
“Don’t you DARE give me the Nimoy face!”  
The Cheat held steadfast in his accusations.  
“Okay! Fine! I’m jealous of Strong Sad! Are you happy?”  
The Cheat took pity on his owner and asked if a trip to the cloughb would cheer him up.  
“Go to Club Technochocolate? Alone? Do you know how badly my image would suffer if my loser little brother showed up with an awesome date and I didn’t? I couldn’t bear to show my face or leopard print briefs in there ever again!”  
The Cheat offered a suggestion.  
“Disguise? Hmm…” Strong Bad began to smile deviously. “The Cheat, I gots an idea!”

It really was brilliant. The disguise had worked wonders before on Halloween. And with a few alterations, it would be perfect for a night out at the Club. A red wig, a rope, some cool, cool glasses, and a coat rack… ingenious! Strong Bad completed the illusion by taking an old fleece blanket and tying it around the coat rack, just above his head.  
“Look out, Club Techno Choco,” Strong Bad said in a heavy southern drawl, “here comes Sharpdene!”

As was usually the case on Friday nights, the Club was packed with familiar faces from around Free Country, USA.  
Strong Sad was coyly making passes at Pom Pom from the corner while the Big Orange balloon man was cutting a piece of flashing, multi-colored neon rug.  
Marzipan and Homestar, celebrating their longest relationship in over ten years (approximately four weeks and counting), were trying out a couples dance. It was… going poorly.  
“Homestar, stop stepping on my feet.”  
“Oops. Sorry. I can’t even see your feet right now.”  
“It’s fine. Just be careful.”  
“You’re not going to break up with me again, are you?”  
“No, I’ve decided that abandoning our relationship on a whim won’t get us anywhere. Besides, you’re the only person in this town who isn’t unappealing, taken or not into girls.”  
“Hooray! I’m the lowest common denominator!”

Off in another corner was the power couple of Coach Z and Bubs. The members of the Two-o Duo were supposed to be up on stage, but DJ Teh Cheat was mysteriously absent, and the Goblin (the club’s newly acquired other resident DJ) didn’t know any of their tracks. So instead the old men gorged themselves on piña coladas.  
“Boy, I tell ya Bubsy,” said Coach Z, “these coladas beat drinkin’ mouth-warsh any day o’ the week!”  
“Yeah. Good thing you stopped drinking that Listerine. It ain’t good for you.  
“Aw, you’re so cute when you’re concerned abrat my health.”  
“Save it for the green room, green boy! We got a show to do!”

Strong Bad peeked through the drapes of his dress at the club ahead. Standing outside was the bouncer, Strong Mad, who had for once NOT fallen asleep on the job.  
“Just keep calm and try to stay in character,” Strong Bad whispered to himself.  
Walking up to the door. Strong Bad’s big bro seemed a lot more imposing than usual. “NAME PLEASE,” Strong Mad said.  
Strong Bad put on his drawl. “Sharpdene, I’m uh… with the band.”  
Strong Mad looked over his “list”: a greasy bag of mini burgs from Blubb- O’s. “YOU’RE NOT ON THE LIST!”  
Luckily, Strong Bad had brought along The Cheat as a countermeasure. The Cheat, rocking his DJ headphones, walked up to Strong Mad to vouch for Sharpdene.  
“Duh?”  
The Cheat concocted an elaborate backstory which I assure you was about as coherent as you could make a story only using variations on the word “meh”.  
“FINE BY ME. ENJOY YOUR NIGHT,” said Strong Mad, unclipping the velvet rope to let in The Cheat and Sharpdene.  
“Thanks for having my back, The Cheat,” whispered Strong Bad. The Cheat nodded in acknowledgement and went up to the DJ booth to tell the Goblin he could take five.  
Strong Bad wandered onto the dance floor. He was itching to bust some moves, but unfortunately he had trouble seeing through the curtains. While attempting to perform the electric slide, he accidentally bumped into Pom Pom, who was a bit peeved with the coat rack for throwing off his groove.  
“Oops. Uh… sorry big boy,” said Sharpdene, “I didn’t see you there. I’m, uh, legally blind in both eyes.”  
Pom Pom didn’t buy that a blind woman wouldn’t carry a cane into the club, or come into a loud club at all. Nevertheless he apologized, introduced himself and asked her name.  
“I’m Sharpdene, nice to meetcha. Say, care to dance?”  
Pom Pom politely declined.  
“Aw, that’s a shame. Why not?”  
Pom Pom quickly pointed out Strong Sad, watching from the corner.  
“Oh, is that your boyfriend? I remember him from last Halloween! He seems so… depressed. Why isn’t he dancing?”  
Pom Pom shrugged.  
Strong Bad smiled deviously again. “Hold on a hot second. I gots an idea,” said Sharpdene.  
Strong Bad walked over to Strong Sad and started making small talk. “Hey honey, remember me?”  
Strong Sad searched his memory. “Sharpdene? I haven’t seen you since last Halloween! What are you doing here?”  
“Can’t a gal just have fun at the club by herself? Listen, not that it’s any o’ my beeswax, but, uh, your boyfriend over there? He’s feeling pretty lonely dancing with himself like Billy Dee Williams.”  
“Dancing with Myself is a Billy Idol song.”  
“Yeah, yeah, American Idol, whatever. The point is, why don’t you go out there with him? I’m sure he’d love to dance with ya.”  
“I’m, uh… not that good at dancing. I’d just embarrass myself.”  
“Oh, please, you’re embarrassing your man by leaving him out on the floor alone.”  
“I don’t feel comfortable.”  
“You’ll get used to it.” Sharpdene pushed Strong Sad away from the wall and into Pom Pom. The couple awkwardly looked at one another for a few seconds and then started dancing like Vincent and Mia from Pulp Fiction. Which is to say, not well, but with genuine chemistry.  
Strong Bad walked off snickering at Strong Sad’s poor attempts at dancing. About halfway across the floor he realized he had also diverted the attention of the club away from himself. He stopped snickering after realizing this.  
Strong Bad thought to go out on the floor and dance as well, but A. didn’t have a partner, and B. didn’t really feel like it anyhow. So instead he opted to try and cut in with the other couples.  
Homestar and Marzipan were somehow in sync for once, and enjoying themselves immensely. Then Sharpdene came up.  
“Excuse, me ma’am, what’s your name?”  
“Marzipan. And you are…?”  
“Sharpdene. I’m new in town.”  
“Sharpdene? Wait a minute, I got a call from someone named Sharpdene last year. But… I thought that was just Strong Bad with a bad southern accent pulling a prank on me. You’re not really here to fight, are you?”  
“What? Oh, heavens, no. I forgot all about that.” He honestly HAD forgotten all about the origins of his Sharpdene character. “Besides, Strong Bad got me a tray of brownies, so it’s all good. Anyway, mind if I cut in?”  
“Normally I’d consider that offer, but I have a boyfriend.”  
“You do?” asked Homestar. “I thought we had an understanding!”  
“My boyfriend is you, Homestar.”  
“Oh. Right.”  
“So what?” said Sharpdene. “You’ve broken up with Homestar tons of times! ...is what my roommate Strong Bad told me.”  
“Well,” said Marzipan, “you can tell your roommate that until further notice, I’m not breaking up with my boyfriend.”  
“Yeah!” said Homestar. “I’m still the boyfriend, right?”  
“Yes.”  
“Yeah!”  
“Understandable,” said Sharpdene, with a sigh. “I’m gonna go see if Bubsy over there is up for some action. Bye bye now.” Strong Bad left feeling a bit desperate. He wasn’t getting between Pom Pom and Strong Sad, or Marzipan and Homestar, and the only options left were the Cheat (which would be way too weird) the Goblin (who was already married to the Jibblies Painting), and two old, drunk, gay dudes. Well, nothing ventured, nothing gained.

Coach Z was almost fall-down drunk and trying to drink water to sober up. Bubs was holding him up straight, though he was also a little tipsy.  
“My palms are sweaty, knees weak, arms are heavy…” Coach Z said.  
“Don’t throw up on your sweats, Coach. Those are your only clothes,” said Bubs.  
“I’m trying!”  
Sharpdene had caught the two at a bad time. “You two need help?”  
“No thanks, we… we got this,” said Bubs.  
“Well if there’s anything I can do for you…”  
“Actually, I got an idea. Help me get the Coach into the bathroom.”  
Strong Bad was a little concerned about what he had gotten himself into, but agreed to help for the sake of Coach Z’s continued existence. “Uh… okay.” Bubs slung Coach Z over his shoulders and Strong Bad held the Coach’s legs up.

Five minutes and a series of horrid retching noises later, Coach Z was now sobered up enough to stand, and with minimal damage to his outfit! “Gash, ma’am, thanks fer da help. What’s yer name?” asked Coach Z.  
“Sharpdene,” said Strong Bad, trying to ignore the horrid puke smell.  
“Well, thanks a million, Sharpdene!” said Bubs. “Now we can get on stage and re-re-reunite the Two-o Duo!”  
“Let’s go out there and knock ‘em dead, big poppa!” said the Coach.  
Bubs and Coach Z left the bathroom, holding each other up. “Oh, I LOVE it when you call me that!”  
Strong Bad was too disgusted and disappointed to leave the bathroom. Sharpdene was meant to be the life of the party and she ended up being everybody’s third wheel. Strong Bad leaned against the wall, feeling left out and depressed.  
“Man,” he said to himself, “can’t a gal just have fun at the club by herself?”  
To Strong Bad’s surprise, his question got answered, albeit incoherently: “I’m a fish stick lookin’ for a chicken biscuit!” Turning around, Strong Bad found Homsar standing in the doorway.  
Strong Bad slipped back into character. “Oh! Hi there, I’m Sharpdene. Who are you?”  
Homsar walked into the bathroom and somehow onto the ceiling. “The captain of the gravy train is on the field!”  
“Your… shirt says Homsar. Is that your name?”  
“Sure as a monkey’s fiddle.”  
“I’ll take that as a yes. So, what ‘s happening?”  
“I got a skeleton key in my basement.”  
“Oh. I see. I think. I have no idea what you’re talking about.”  
Homsar flipped back right side up. “My popsicle is ready for summer.”  
“Are… you coming onto me?”  
Homsar, in a rare display of flirtation, waggled his eyebrows. “If only, if only!”  
Strong Bad wasn’t exactly sure how to feel about this. “Oh boy. Uh… listen. No offense, but I’ve never actually done something like this before. And uh, I’d kinda like my first time to be with a lady. Of the female persuasion.”  
Homsar was nonplussed by this. “One hot dish for table two!” Summoning some kind of weird mystical energy, Homsar began floating in the air. Spinning in circles, Homsar was enveloped by a blue glow and his body was remolded into that of a modestly hot woman.  
Strong Bad was amazed. “Wow.”  
“How about a ticket to the boat show?” asked Homsar.  
“I’d love to go to the boat show. Where is it?”  
Female Homsar and Strong Bad went into a nearby bathroom stall. Clearly, there was sex to be had in the future. Unfortunately for Strong Bad, this meant having to blow his cover, since you can’t really lie about your appearance when you’re naked.  
“Look, before we go any further, I have to confess something.” Strong Bad dropped the accent and removed his costume. “My name isn’t Sharpdene. It’s Strong Bad. I’d understand if this got weird.”  
Female Homsar was once again nonplussed. “Any way the wind blows.”  
Strong Bad was relieved and kind of turned on. He nearly tore off his pants and underwear, revealing a decently sized cock and balls that were currently hard as steel. “Oh, yeah. Keep reciting Queen lyrics!”  
“And another one rides the bus!” Female Homsar took off her dress. Long brown hair, big bouncy breasts, curves for days, and smooth, white skin… she looked exactly the way Strong Bad had pictured it. Except for one minor detail. Homsar still had some holdovers from her male body, namely a penis and balls.  
Strong Bad was a bit unnerved, but then Homsar turned around and spread her legs, revealing that she did have a vagina. Strong Bad’s brain tried to reconcile this, and ultimately he decided it was fine. He was having sex for the first time, and he wasn’t going to question to biology of the girl on the receiving end. “She’s a girl. Just go with it,” he thought to himself.  
It took some time for Strong Bad to get used to the thrusting rhythm, but once he had it down, he and Homsar were moaning loudly. Fortunately the music in the club was so loud that no one could hear them.  
Strong Bad couldn’t keep up the thrust for too long, but he had lasted a decent while for his first time: approximately two minutes before he completely blew his load. Homsar reached climax fairly easily as well. Strong Bad pulled himself out of Homsar’s pussy, feeling strange but somehow satisfied. And he only bonked his head against the wall five times!  
“Was it good for you too, baby?” asked Strong Bad, coming down from his sexual high.  
Homsar’s bizzare physiology continued to throw curveballs at Strong Bad. Before Homsar could even respond to Strong Bad’s question, her belly began to inflate like a party balloon. “Oh no, I think I got a honey bun in my cabbage patch!”  
“Wait, what? You’re… you’re pregnant? Oh boy, this isn’t good. I’m too young to be an illegitimate father!”  
“I’m going on vacation to the red cross!” Homsar somehow walked through the walls of the club, running away in a blind panic to the nearest hospital.  
“Homsar! Wait! Come back! I’m sorry for what I did! Kinda! Aw man!”  
The rest of the club had been drawn into the bathroom by the ruckus. Strong Bad’s cover had been completely obliterated.  
“Uh, look, I can explain-”  
“Please put on some clothes first,” said Marzipan.  
Strong Bad hurriedly went back into the stall and put his pants back on, before coming back out to face the music. “So, nobody probably noticed, but… Sharpdene was me the whole time.  
“We know,” replied everyone else.  
“You do?”  
“That pink towel dress barely covered your head, We could see the rest of you,” said Strong Sad.  
“And the southern accent didn’t really disguise your voice.” said Bubs.  
“Even I could tell,” said Homestar. “Those boots you’re wearing are a dead giveaway.”  
“Well. Now I feel bad and dumb. So you guys were just indulging me this whole time?” asked Strong Bad.  
“We thought you was going through some kinda transvestite phase.” said Coach Z.  
“So what happened?” asked Marzipan.  
“Well, I wanted to come to the club but I was afraid of being overshadowed by Strong Sad and Pom Pom-”  
“You were jealous of me?” asked Strong Sad.  
“Don’t get used to it. Anyway, I thought I’d disguise myself and become the life of the party, but I just ended up being a wallflower. After I helped Coach Z into the bathroom and he left with Bubs, Homsar came in and started hitting on me. I told him I was interested in ladies, so he turned into a lady and we had sex and then she got pregnant and disappeared and you all think I’m making this up, don’t you?”  
“Actually,” said Bubs, “I have seen Lady Homsar before.”  
“Same,” said Coach Z.  
“Same,” said Homestar.  
Pom Pom bubbled in agreement.  
“Me too,” said Marzipan.  
“None of you are wondering how she got pregnant so quickly?” asked Strong Bad.  
“It’s Homsar,” said Strong Sad. “It wouldn’t surprise me.”  
“You being with a lady, on the other hand…” said Bubs.  
Strong Bad was offended. “I did too have sex with her. I can prove it too!” said Strong Bad, going back into the stall to retrieve Homsar’s dress. “See? This is the dress she took off, before she… took off.” Strong Bad would have ordinarily bragged for several minutes about something like this, but his heart wasn’t in it a the moment.  
“Well,” said Homestar, “Congratulations on losing your virginity and becoming a father in the same night.”  
“Thanks, Homeslice. I just… don’t know if she’ll ever want to talk to me again after this.”  
Strong Sad, being a helpful younger brother for once, spoke up. “I think I can get you in touch with her if you need.”

The next day, back at the House of Strong, Strong Bad tapped his boxing gloves on his desk, waiting for the voice to pick up on the other end of his Nokia. After a long while, Strong Bad heard the familiar voice of Homsar on the other end.  
“Hello?” asked Homsar.  
“Hey, uh, Homsar?”  
“Oh, hello there Strong Bad.”  
“Wait, since when could you talk normal? Like without some mysterious translation artifact?”  
“I’m not sure. I’ve always been more articulate over the phone.”  
“Well, uh, I wanted to check in on you… see if you’re still upset or anything.”  
“Why would I be upset? I came on to you, remember?”  
“Well, you left in such a hurry last night.”  
“Of course I left in a hurry. I was having a baby!”  
“Yeah, sorry about that. In retrospect, I probably should brought some kind of protection.”  
“Listen, I wasn’t entirely honest with you last night. Things get a bit lonely around my home, and I was just wondering to myself what it would be like to have a kid.”  
“And how’s that working out?”  
“Alright, I suppose. The little man is a bit of a troublemaker.”  
“Takes after his dad, huh?”  
“Yeah.”  
“So, what happens with us now? Do we raise the kid together?”  
“Well, I’m fine raising little Reggie on my own, but I wouldn’t mind a little help.”  
“Reggie? That’s the name you went with?”  
“You try coming up with a boy’s name on the spot!”  
“So, out of curiosity, have you turned back into a guy, or-”  
“I switch back and forth. But, I’m currently a male.”  
“So, I guess that makes me a bicycle.”  
“You mean bisexual?”  
“Yeah, that. So, maybe I could come see you tomorrow.”  
“I’d like that.”  
“Okay. Bye, sugarbob.  
“Bye bye, Sharpdene!”  
Strong Bad hung up. Maybe Sharpdene did turn out to be the life of the party after all. Strong Bad’s night was definitely the most eventful night of his entire life. Everything was different now. He wasn’t sure if he was ready for it, but oh well. Nothing ventured, nothing gained.


End file.
